Omiganan is the Common International Denomination (CID) for the peptide H-Ile-Leu-Arg-Trp-Pro-Trp-Trp-Pro-Trp-Arg-Arg-Lys-NH2 (SEQ ID NO 1) that is mostly used in the form of its pentahydrochloride (5 HCl) salt. Omiganan is a cationic antimicrobial peptide. Recent research has also shown that it may play a role in the inflammatory response. Omiganan, in in vitro assay, demonstrated a rapid bactericidal activity against micro-organisms that colonize the skin and that may play a role in the pathogenesis of inflammatory lesions. Omiganan pentachloride is moreover currently in a Phase II-III for treatment of severe acne and in a Phase III clinical trial for the prevention of central venous catheter-related bloodstream infections.
Omiganan can be produced via a linear peptide synthesis wherein the respective amino acids are consecutively added to a growing peptide chain. These processes are unsatisfactory as to yield and purity of the desired peptide Omiganan.
The present invention now makes available an improved synthesis for the peptide Omiganan.
U.S. Pat. No. 5,262,567 discloses the use of a compound including a guanidine group and an unsubstituted tetraphenylborate ion as intermediate in the synthesis of peptides. As an example, the synthesis of the compound formed by arginine and tetraphenylborate (TPB) and its use in the synthesis of the peptide Boc-Leu-Arg-OH is described.
WO 99/65506 A discloses pharmaceutical compositions containing cationic peptides including the cationic peptide MBI 11B20CN which contains the amino acid sequence of Omiganan.